A trial license can be extended up to five times from the Jira app manager. Clear the license field, update, then start a new trial.
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Go to your Jira UPM screen - https://your.jira/plugins/servlet/upm
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Find the Agile Tools & Filters app and edit the existing license key
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Manually clear the license field and select the Update button
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Use the Free Trial button to get a new trial license
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The new license will be generated and trial will be extended by 30 extra days.